JPH11228858A - Condensed azo pigment derivative and pigment composition containing the same - Google Patents
Condensed azo pigment derivative and pigment composition containing the sameInfo
- Publication number
- JPH11228858A JPH11228858A JP2712198A JP2712198A JPH11228858A JP H11228858 A JPH11228858 A JP H11228858A JP 2712198 A JP2712198 A JP 2712198A JP 2712198 A JP2712198 A JP 2712198A JP H11228858 A JPH11228858 A JP H11228858A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- formula
- compound
- azo
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、縮合アゾ顔料の誘
導体及びそれの顔料用途への応用に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a derivative of a condensed azo pigment and its application to pigment use.
【０００２】[0002]
【従来の技術】塗料や印刷インキなど、顔料を含有する
非水性分散系において、顔料はしばしば凝集し、沈降、
粘度の増加、着色力の低下、他顔料と混合した際の色分
かれなど、種々の問題を引き起こす。このような流動性
や非凝集性の低下に伴う問題を解決する目的でこれまで
も、フタロシアニン系及びキナクリドン系顔料を中心に
数多くの提案がなされている。例えば、特公昭 41-2466
号公報や特公昭 50-4019号公報に記載のように、顔料の
スルホン化物又はその金属塩を混和する方法、特公昭 3
8-2713号公報や特公昭 39-16787 号公報に記載のよう
に、置換アミノメチル誘導体を混和する方法、米国特許
第 2,761,868号明細書や特開昭 55-108466号公報に記載
のように、フタルイミドメチル誘導体を混和する方法な
どが知られている。しかしながらこれらの方法では、顔
料の非凝集性が改善される傾向は認められるものの、白
色顔料と混ぜたときの色分かれが依然として大きく、十
分満足しうるには至っていない。BACKGROUND OF THE INVENTION In non-aqueous dispersions containing pigments, such as paints and printing inks, the pigments often agglomerate, settle,
It causes various problems such as an increase in viscosity, a decrease in coloring power, and color separation when mixed with other pigments. Numerous proposals have been made mainly on phthalocyanine-based and quinacridone-based pigments for the purpose of solving the problems associated with such a decrease in fluidity and non-aggregation. For example, Japanese Patent Publication No. 41-2466
As described in Japanese Patent Publication No. JP-A-50-4019 and JP-B-50-4019, a method of admixing a sulfonated pigment or a metal salt thereof,
As described in 8-2713 and JP-B-39-16787, a method of mixing a substituted aminomethyl derivative, as described in U.S. Pat.No. 2,761,868 and JP-A-55-108466, A method of mixing a phthalimidomethyl derivative is known. However, in these methods, although the tendency of the non-agglomeration of the pigment to be improved is recognized, the color separation when mixed with a white pigment is still large and has not been sufficiently satisfactory.
【０００３】また、特開平 1-213366 号公報及び特公平
1-34268号公報には、上記の欠点を改良する目的で開発
された顔料誘導体が開示されている。しかし、これらの
顔料誘導体を用いてもなお、十分満足しうるには至って
いない。[0003] Also, Japanese Patent Application Laid-Open No. Hei 1-213366 and
JP-A 1-34268 discloses a pigment derivative developed for the purpose of improving the above-mentioned disadvantages. However, the use of these pigment derivatives has not been sufficiently satisfactory.
【０００４】[0004]
【発明が解決しようとする課題】そこで、顔料の流動性
及び非凝集性の低下などに伴う種々の問題を工業的有利
に解決する手段の開発が、強く望まれている。Therefore, there is a strong demand for the development of means for industrially solving various problems associated with a decrease in the fluidity and non-aggregation properties of pigments.
【０００５】本発明の目的は、有機顔料と混合したとき
に、流動性及び非凝集性を改良しうる化合物を提供し、
さらにはその化合物を用いて、流動性及び非凝集性に優
れた顔料組成物を提供することにある。[0005] It is an object of the present invention to provide a compound which, when mixed with an organic pigment, can improve flow and non-agglomeration,
It is still another object of the present invention to provide a pigment composition having excellent fluidity and non-aggregation property using the compound.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、かかる目
的を達成すべく鋭意研究を行った結果、ある種の縮合ア
ゾ顔料から誘導される化合物を見出し、そしてこの化合
物を有機顔料と混合することにより、上記の目的が達成
できることを見出し、本発明を完成するに至った。Means for Solving the Problems The present inventors have conducted intensive studies to achieve such an object, and as a result, have found a compound derived from a kind of condensed azo pigment, and mixed this compound with an organic pigment. As a result, the present inventors have found that the above object can be achieved, and have completed the present invention.
【０００７】すなわち本発明は、遊離酸の形で表したと
きに、下式（Ｉ）に相当するスルホンアミド化アゾ化合
物を提供するものである。That is, the present invention provides a sulfonamidated azo compound corresponding to the following formula (I) when expressed in the form of a free acid.
【０００８】 [0008]
【０００９】式中、Ｒ1 及びＲ2 は互いに独立に、それ
ぞれ置換されてもよい炭素数２０以下の脂肪族炭化水素
若しくは芳香族炭化水素の残基を表すか、又は両者が一
緒になって、それらが結合する窒素原子とともに、さら
に窒素、酸素及び硫黄から選ばれる異項原子を含んでも
よい複素環を形成し、ｋは１〜６の整数を表し、 ｍは
０.5〜３、そしてｎは０.5〜３.5の数を表すが、ｍとｎ
の合計は１〜５である。In the formula, R 1 and R 2 independently represent a residue of an aliphatic hydrocarbon or an aromatic hydrocarbon having 20 or less carbon atoms which may be substituted, or a combination of both. Together with the nitrogen atom to which they are attached, form a heterocyclic ring which may further contain heteroatoms selected from nitrogen, oxygen and sulfur, k represents an integer of 1 to 6, m is 0.5 to 3, and n represents a number from 0.5 to 3.5, and m and n
Is 1 to 5.
【００１０】このスルホンアミド化アゾ化合物は、有機
顔料と混合して用いることにより、その有機顔料の特
性、特に流動性及び非凝集性を改善するのに有効であ
る。そこで本発明はまた、有機顔料及び上記式（Ｉ）に
相当するスルホンアミド化アゾ化合物を含有してなる顔
料組成物をも提供する。When the sulfonamido azo compound is used in a mixture with an organic pigment, it is effective in improving the properties of the organic pigment, particularly, fluidity and non-aggregation. Therefore, the present invention also provides a pigment composition comprising an organic pigment and a sulfonamidated azo compound corresponding to the above formula (I).
【００１１】[0011]
【発明の実施の形態】上記式（Ｉ）において、Ｒ1 及び
Ｒ2 はそれぞれ、炭素数２０以下の脂肪族炭化水素又は
芳香族炭化水素の残基であることができ、これらはさら
に置換基を有してもよい。ここでいう脂肪族炭化水素残
基は、アルキルのような飽和でも、またアルケニルやア
ルキニルのような不飽和でもよいが、好ましいものは、
置換されてもよい炭素数１〜６のアルキルである。芳香
族炭化水素残基には、それぞれ置換されてもよいフェニ
ルやナフチルなどが包含される。これらの炭化水素残基
に結合してもよい置換基としては、無置換の又は、炭素
数１〜６のアルキル若しくは炭素数１〜６のヒドロキシ
アルキルで１又は２回置換されたアミノ、無置換の又
は、ヒドロキシ若しくは炭素数１〜６のアルコキシで置
換された炭素数１〜６のアルコキシなどを挙げることが
できる。もちろん、Ｒ1 及び／又はＲ2 がアルキルのよ
うな脂肪族炭化水素残基である場合は、そこにフェニル
などの芳香族炭化水素残基が置換することもでき、一
方、Ｒ1 及び／又はＲ2 がフェニルやナフチルのような
芳香族炭化水素残基である場合は、これらのフェニルや
ナフチルには、炭素数１〜６のアルキルなどの脂肪族炭
化水素残基が置換することもできる。BEST MODE FOR CARRYING OUT THE INVENTION In the above formula (I), R 1 and R 2 may each be a residue of an aliphatic hydrocarbon or an aromatic hydrocarbon having 20 or less carbon atoms, and these are further substituted with a substituent. May be provided. As used herein, the aliphatic hydrocarbon residue may be saturated such as alkyl, or unsaturated such as alkenyl or alkynyl.
It is a C1-C6 alkyl which may be substituted. Aromatic hydrocarbon residues include phenyl and naphthyl, each of which may be substituted. Examples of the substituent that may be bonded to these hydrocarbon residues include unsubstituted or amino substituted once or twice with alkyl having 1 to 6 carbons or hydroxyalkyl having 1 to 6 carbons, unsubstituted amino. Or alkoxy having 1 to 6 carbon atoms substituted by hydroxy or alkoxy having 1 to 6 carbon atoms. Of course, when R 1 and / or R 2 is an aliphatic hydrocarbon residue such as alkyl, it may be substituted with an aromatic hydrocarbon residue such as phenyl, while R 1 and / or R 2 may be substituted. When R 2 is an aromatic hydrocarbon residue such as phenyl or naphthyl, these phenyl or naphthyl can be substituted by an aliphatic hydrocarbon residue such as alkyl having 1 to 6 carbon atoms.
【００１２】またＲ1 及びＲ2 は、両者が一緒になっ
て、それらが結合する窒素原子とともに複素環を形成す
ることもできる。この場合の複素環は、式（Ｉ）中でＲ
1 及びＲ2 が直接結合するように表示されている窒素原
子以外に、さらに異項原子を含んでもよく、この場合の
異項原子としては、窒素、酸素及び硫黄が挙げられる。
このような−ＮＲ1Ｒ2に相当する複素環残基としては、
ピロリジンの１価基である１−ピロリジニル、ピペリジ
ンの１価基であるピペリジノ、ピペラジンの１価基であ
る１−ピペラジニル、モルホリンの１価基であるモルホ
リノ、ペルヒドロ−１，４−チアジンの１価基であるペ
ルヒドロ−１，４−チアジン−４−イル、ペルヒドロア
ゼピンの１価基であるペルヒドロアゼピン−１−イルな
どが例示される。これらの複素環はまた、場合により低
級アルキルなどで置換されていてもよく、このような枝
分かれした複素環残基の具体例としては、ピペコリンの
１価基である２−、３−又は４−メチルピペリジノなど
を挙げることができる。Further, R 1 and R 2 may be taken together to form a heterocyclic ring together with the nitrogen atom to which they are bonded. The heterocyclic ring in this case is represented by R in the formula (I)
Besides 1 and the nitrogen atom to which R 2 is displayed so as to bind directly, further may contain a hetero atom, as a hetero atom in this case include nitrogen, oxygen and sulfur.
As such a heterocyclic residue corresponding to —NR 1 R 2 ,
1-pyrrolidinyl, a monovalent group of pyrrolidine, piperidino, a monovalent group of piperidine, 1-piperazinyl, a monovalent group of piperazine, morpholino, a monovalent group of morpholine, and monovalent of perhydro-1,4-thiazine Examples thereof include perhydro-1,4-thiazin-4-yl which is a group, and perhydroazepin-1-yl which is a monovalent group of perhydroazepine. These heterocycles may be optionally substituted by lower alkyl or the like, and specific examples of such a branched heterocycle residue include 2-, 3- or 4- which is a monovalent group of pipecoline. Methyl piperidino and the like can be mentioned.
【００１３】式（Ｉ）中のＣkＨ2k で表されるアルキレ
ンは、通常直鎖であるが、ｋが２以上の場合は分岐して
いても構わない。The alkylene represented by C k H 2k in the formula (I) is usually straight-chain, but may be branched when k is 2 or more.
【００１４】式（Ｉ）で示されるスルホンアミド化アゾ
化合物は、下式（II）The sulfonamide azo compound represented by the formula (I) is represented by the following formula (II)
【００１５】 [0015]
【００１６】に相当するＣ.Ｉ.ピグメントレッド 242と
して公知の顔料を原料とし、それ自身公知の方法に準じ
て、製造することができる。例えば、Ｃ.Ｉ.ピグメント
レッド242にクロロスルホン酸を作用させ、必要により
クロロスルホニルの一部を加水分解した後、これに、式
ＮＨ2ＣkＨ2kＮＲ1Ｒ2 で示されるジアミノ化合物を反
応させることによって、式（Ｉ）で示されるスルホンア
ミド化アゾ化合物を製造することができる。A pigment known as CI Pigment Red 242 corresponding to the above can be used as a raw material, and can be produced according to a method known per se. For example, after chlorosulfonic acid is allowed to act on CI Pigment Red 242 to partially hydrolyze chlorosulfonyl if necessary, a diamino compound represented by the formula NH 2 C k H 2k NR 1 R 2 is added thereto. By reacting, a sulfonamidated azo compound represented by the formula (I) can be produced.
【００１７】クロロスルホン酸との反応は、例えば、必
要により有機溶剤を用い、Ｃ.Ｉ.ピグメントレッド 242
と、それに対して１〜１０モル倍のクロロスルホン酸と
を、−１０°〜＋１５０℃の温度で接触させることによ
り、行うことができる。必要によりさらに、塩化チオニ
ル、オキシ塩化リン、五塩化リンのようなハロゲン化剤
を加えてもよい。こうして得られる反応生成物とジアミ
ノ化合物との反応は、例えば、反応生成物とジアミノ化
合物又はその塩とを、水又は有機溶媒中、０〜１５０℃
の温度で接触させることにより、行うことができる。The reaction with chlorosulfonic acid can be carried out, for example, using an organic solvent, if necessary, using CI Pigment Red 242.
And 1 to 10 times the molar amount of chlorosulfonic acid at a temperature of -10 ° to + 150 ° C. If necessary, a halogenating agent such as thionyl chloride, phosphorus oxychloride or phosphorus pentachloride may be added. The reaction between the reaction product thus obtained and the diamino compound is performed, for example, by reacting the reaction product with the diamino compound or a salt thereof in water or an organic solvent at 0 to 150 ° C.
The contact can be carried out at the following temperature.
【００１８】前記式（Ｉ）におけるｍ及びｎ並びにその
合計は、使用するクロロスルホン酸の量と反応温度によ
って適宜選択することができ、またｍとｎの割合は、ハ
ロゲン化剤の添加の有無及び量、Ｃ.Ｉ.ピグメントレッ
ド 242とクロロスルホン酸との反応生成物を水又は有機
溶剤中に加え、溶液若しくは懸濁液とする際の保温温度
又は保温時間、それに反応させるジアミノ化合物又はそ
の塩の量、その際の反応温度などによって、適宜選択す
ることができる。M and n in the above formula (I) and the total thereof can be appropriately selected depending on the amount of chlorosulfonic acid used and the reaction temperature, and the ratio of m and n is determined by the presence or absence of the halogenating agent. And the amount thereof, the reaction temperature of the reaction product of CI Pigment Red 242 and chlorosulfonic acid in water or an organic solvent to form a solution or a suspension, or a diamino compound or a diamino compound to be reacted therewith. It can be appropriately selected depending on the amount of the salt, the reaction temperature at that time, and the like.
【００１９】上記の反応において用いられるジアミノ化
合物としては、Ｎ，Ｎ−ジメチルアミノエチルアミン、
Ｎ，Ｎ−ジエチルアミノエチルアミン、Ｎ，Ｎ−ジベン
ジルアミノエチルアミン、Ｎ，Ｎ−ジメチルアミノプロ
ピルアミン、Ｎ，Ｎ−ジエチルアミノプロピルアミン、
Ｎ，Ｎ−ジエタノールアミノプロピルアミン、Ｎ，Ｎ−
ジブチルアミノプロピルアミン、Ｎ，Ｎ−ジメチルアミ
ノヘキシルアミン、Ｎ−エチル−Ｎ−（β−アミノエチ
ル）−ｍ−トルイジン、Ｎ−アミノエチルピロリジン、
Ｎ−アミノメチルピペリジン、Ｎ−アミノエチルピペリ
ジン、Ｎ−アミノメチル−４−ピペコリン、Ｎ−アミノ
プロピル−２−ピペコリン、Ｎ−アミノエチルモルホリ
ン、Ｎ−アミノエチルピペラジンなどが例示される。The diamino compound used in the above reaction includes N, N-dimethylaminoethylamine,
N, N-diethylaminoethylamine, N, N-dibenzylaminoethylamine, N, N-dimethylaminopropylamine, N, N-diethylaminopropylamine,
N, N-diethanolaminopropylamine, N, N-
Dibutylaminopropylamine, N, N-dimethylaminohexylamine, N-ethyl-N- (β-aminoethyl) -m-toluidine, N-aminoethylpyrrolidine,
Examples include N-aminomethylpiperidine, N-aminoethylpiperidine, N-aminomethyl-4-pipecholine, N-aminopropyl-2-pipecholine, N-aminoethylmorpholine, N-aminoethylpiperazine and the like.
【００２０】式（Ｉ）におけるスルホン酸基は、遊離酸
のまま存在することもでき、また、１〜３価の金属又は
有機アミンと塩を形成した形で存在することもできる。
ここで、塩を構成する１〜３価の金属としては、ナトリ
ウム、カリウム、マグネシウム、カルシウム、ストロン
チウム、バリウム、アルミニウムなどが例示される。ま
た有機アミンとしては、前記のジアミノ化合物のほか、
エチルアミン、プロピルアミン、アミルアミン、ヘキシ
ルアミン、オクチルアミン、ドデシルアミン、ステアリ
ルアミン、ジエチルアミン、ジブチルアミン、トリエチ
ルアミンのような脂肪族アミン類、ピロリジン、ピペコ
リン、ピペリジン、ピペラジン、モルホリンのような複
素環アミン類、アニリン、トルイジンのような芳香族ア
ミン類などが例示される。式（Ｉ）で示される化合物
（遊離酸）の金属又は有機アミン塩は、公知の方法、例
えば、上記遊離酸の水性懸濁液と、金属又は有機アミン
の塩化物水溶液若しくは懸濁液を混合することにより、
容易に得ることができる。The sulfonic acid group in the formula (I) may be present as a free acid or may be present in the form of a salt with a monovalent metal or organic amine.
Here, sodium, potassium, magnesium, calcium, strontium, barium, aluminum and the like are exemplified as the 1-3-valent metal constituting the salt. As the organic amine, in addition to the above diamino compounds,
Heterocyclic amines such as ethylamine, propylamine, amylamine, hexylamine, octylamine, aliphatic amines such as dodecylamine, stearylamine, diethylamine, dibutylamine, triethylamine, pyrrolidine, pipecoline, piperidine, piperazine, and morpholine; Examples thereof include aromatic amines such as aniline and toluidine. The metal or organic amine salt of the compound (free acid) represented by the formula (I) can be prepared by a known method, for example, by mixing an aqueous suspension of the free acid with an aqueous chloride solution or suspension of the metal or organic amine. By doing
Can be easily obtained.
【００２１】本発明の顔料組成物は、式（Ｉ）のスルホ
ンアミド化アゾ化合物を、それ自身公知の方法で有機顔
料に配合することによって、製造することができる。こ
の組成物において、式（Ｉ）のスルホンアミド化アゾ化
合物は、有機顔料に対し、好ましくは０.5〜３０重量
％、さらに好ましくは１〜２０重量％の範囲で用いられ
る。The pigment composition of the present invention can be produced by blending the sulfonamido azo compound of the formula (I) with an organic pigment by a method known per se. In this composition, the sulfonamido azo compound of the formula (I) is used in an amount of preferably 0.5 to 30% by weight, more preferably 1 to 20% by weight, based on the organic pigment.
【００２２】顔料組成物を構成する有機顔料としては、
縮合アゾ系、ベンズイミダゾロン系、ジアントラキノ
ニル系、アントラピリミジン系、フラバントロン系、ア
ンタントロン系、インダントロン系、ピラントロン系、
ビオラントロン系、イソビオラントロン系、フタロシア
ニン系、キナクリドン系、キノフタロン系、ジケトピロ
ロピロール系、ジオキサジン系、イソインドリノン系、
ペリノン系、ペリレン系、チオインジゴ系などの各顔料
が例示される。これらのなかでも、縮合アゾ系顔料に対
して、本発明の式（Ｉ）に相当する化合物は、最も有利
に用いられる。The organic pigments constituting the pigment composition include:
Condensed azo, benzimidazolone, dianthraquinonyl, anthrapyrimidine, flavantron, antanthrone, indanthrone, pyranthrone,
Biolanthrone, isobiolanthrone, phthalocyanine, quinacridone, quinophthalone, diketopyrrolopyrrole, dioxazine, isoindolinone,
Examples of the pigment include perinone pigments, perylene pigments, and thioindigo pigments. Among these, the compound corresponding to the formula (I) of the present invention is most advantageously used for the condensed azo pigment.
【００２３】縮合アゾ系顔料としては、Ｃ.Ｉ.ピグメン
トイエロー 93、94、95、128 及び166、Ｃ.Ｉ.ピグメン
トレッド 144、166、214、220、221 及び 242、Ｃ.Ｉ.
ピグメントブラウン 23 などが例示される。これらのう
ち、Ｃ.Ｉ.ピグメントレッド242が最も有利に用いられ
る。Examples of the condensed azo pigments include CI Pigment Yellow 93, 94, 95, 128 and 166, CI Pigment Red 144, 166, 214, 220, 221 and 242, and CI Pigment Red.
Pigment Brown 23 and the like. Of these, CI Pigment Red 242 is most advantageously used.
【００２４】有機顔料に式（Ｉ）のスルホンアミド化ア
ゾ化合物を配合する方法としては、例えば、それぞれの
乾燥粉末、プレスケーキ、スラリー等を単に機械的に混
合する方法、ニーダー、ビーズミル、アトライター等、
各種粉砕機で粉砕しながら混合する方法、顔料を水又は
有機溶剤に懸濁させ、式（Ｉ）の化合物を有機溶剤に溶
解した状態で添加することによって、顔料表面に式
（Ｉ）の化合物を沈着させる方法、硫酸のような強い溶
解力を持つ溶剤に顔料と式（Ｉ）の化合物を溶解して、
水のような貧溶媒により共沈させる方法などが挙げられ
る。As a method of blending the sulfonamido azo compound of the formula (I) with the organic pigment, for example, a method of simply mechanically mixing each dry powder, press cake, slurry, etc., a kneader, a bead mill, an attritor etc,
A method in which the pigment is suspended in water or an organic solvent, and the compound of the formula (I) is added in a state of being dissolved in the organic solvent, whereby the compound of the formula (I) is added to the surface of the pigment. By dissolving the pigment and the compound of formula (I) in a solvent having a strong dissolving power such as sulfuric acid,
A method of coprecipitating with a poor solvent such as water and the like can be mentioned.
【００２５】[0025]
【実施例】以下、実施例により本発明をさらに詳細に説
明するが、本発明はこれらの実施例によって限定される
ものではない。例中、部及び％は重量基準である。ま
た、スルホン酸基は遊離酸の形で表す。EXAMPLES The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. In the examples, parts and% are based on weight. The sulfonic acid group is represented in the form of a free acid.
【００２６】実施例１ ５０部のＣ.Ｉ.ピグメントレッド 242を１２５部のクロ
ロスルホン酸に加えて６０℃で３時間撹拌し、１３００
部の氷水中に注いだ。得られた懸濁液を濾過後水洗し、
フィルターケーキ１９０部を得た。この反応生成物であ
るフィルターケーキを６６０部の水に加えてスラリー化
し、３０℃で３時間攪拌してクロロスルホニル基の一部
を加水分解した後、８０部のＮ，Ｎ−ジ−ｎ−ブチル−
１，３−プロパンジアミンを加えてさらに３時間撹拌
し、濾過、水洗後、乾燥して、下式の顔料誘導体を得
た。Example 1 50 parts of CI Pigment Red 242 were added to 125 parts of chlorosulfonic acid, stirred at 60 ° C. for 3 hours,
Some of the ice poured into water. The resulting suspension was filtered and washed with water,
190 parts of filter cake were obtained. The reaction product, the filter cake, was added to 660 parts of water to form a slurry, and the mixture was stirred at 30 ° C. for 3 hours to hydrolyze a part of the chlorosulfonyl group, and then 80 parts of N, N-di-n- Butyl-
1,3-propanediamine was added, and the mixture was further stirred for 3 hours, filtered, washed with water, and dried to obtain a pigment derivative represented by the following formula.
【００２７】 [0027]
【００２８】Ｃ.Ｉ.ピグメントレッド 242に導入された
スルホン酸基の平均個数（式（Ｉ）中のｍに相当）とス
ルホンアミド基の平均個数（式（Ｉ）中のｎに相当）
は、氷酢酸溶媒系で過塩素酸滴定による全アミン分の分
別定量、ピリジン／水溶媒系で水酸化ナトリウム滴定に
よる全酸分の分別定量、アルカリ抽出−ガスクロマトグ
ラフ法による残存アミン分の分別定量、及びＮ，Ｎ−ジ
メチルホルムアミド／水溶媒系で硝酸銀滴定による残存
塩素分の分別定量により、求めた。The average number of sulfonic acid groups (corresponding to m in the formula (I)) and the average number of sulfonamide groups (corresponding to n in the formula (I)) introduced into CI Pigment Red 242.
Is the quantitative determination of total amines by perchloric acid titration in a glacial acetic acid solvent system, the quantitative determination of total acids by sodium hydroxide titration in a pyridine / water solvent system, and the differential determination of residual amines by alkali extraction-gas chromatography. , And N, N-dimethylformamide / water solvent system, and the residual chlorine content was determined by silver nitrate titration.
【００２９】実施例２ 実施例１で得られた顔料誘導体１０部を９０部のＣ.Ｉ.
ピグメントレッド 242と混合することにより、顔料組成
物１００部を得た。Example 2 10 parts of the pigment derivative obtained in Example 1 were combined with 90 parts of CI.
Pigment Red 242 to obtain 100 parts of a pigment composition.
【００３０】実施例３ 焼き付け塗料用アミノアルキッド樹脂ワニスに、Ｃ.Ｉ.
ピグメントレッド 242を単独で、又は実施例２で得られ
た顔料組成物を加えて、原色塗料を調製し、その粘度及
び光沢を測定した。また、上記原色塗料と酸化チタン塗
料とを重量比１：１０で混合して淡色塗料を調製し、各
種の性能を調べた。各性能の評価方法は以下のとおりで
あり、結果は表１に示すとおりであった。Example 3 An aminoalkyd resin varnish for baking paint was prepared using CI.
Pigment Red 242 alone or the pigment composition obtained in Example 2 was added to prepare a primary color paint, and its viscosity and gloss were measured. Further, a light-colored paint was prepared by mixing the primary color paint and the titanium oxide paint at a weight ratio of 1:10, and various performances were examined. The evaluation method of each performance was as follows, and the results were as shown in Table 1.
【００３１】粘度： 各原色塗料について、Ｂ型粘度計
を用い、２５℃、３０rpm で測定した。 光沢： 各原色塗料をガラス板に塗布し、焼き付けた
後、６０°−６０°の光沢を測定した。 非凝集性： 各淡色塗料をアート紙上に塗布し、短時間
の乾燥後、塗面の一部を指でこすり、次に塗料を焼き付
け、指でこすった部分とそうでない部分との色濃度を目
視により比較し、以下の基準で評価した。 ◎：差がない。 ○：わずかに差がある。 △：差がよくわかる。 ×：差が歴然としている。 着色力： 各淡色塗料をアート紙上に塗布し、焼き付け
た後の色濃度を、顔料単独の場合を基準（１００）とし
て、目視判定した。Viscosity: The viscosity of each primary color paint was measured using a B-type viscometer at 25 ° C. and 30 rpm. Gloss: After coating each primary color paint on a glass plate and baking, the gloss at 60 ° -60 ° was measured. Non-aggregating: Apply each light-colored paint on art paper, after drying for a short time, rub a part of the painted surface with a finger, then bake the paint, and determine the color density of the part rubbed with the finger and the part that is not They were compared visually and evaluated according to the following criteria. A: There is no difference. ：: There is a slight difference. Δ: Difference is clearly understood. ×: The difference is obvious. Coloring power: Each light-colored paint was applied on art paper, and the color density after baking was visually determined using the pigment alone as a reference (100).
【００３２】[0032]
【表１】 [Table 1]
【００３３】[0033]
【発明の効果】本発明によれば、有機顔料と混合して非
水性分散系とした場合に優れた効果を発揮する化合物
（顔料誘導体）が提供される。したがって、この顔料誘
導体を有機顔料とともに含有してなる本発明の顔料組成
物は、塗料用、印刷インキ用、プラスチック着色用、捺
染用などの各種用途に優れた顔料適性をもって用いるこ
とができ、とりわけ、塗料用又は印刷インキ用の非水性
分散系において、有機顔料を単独で用いた系に比べ、分
散粘度が低下し、良好な流動性を示すとともに、色分か
れもなく、着色力が高く、印刷物又は塗膜の光沢がよ
く、また透明度も高い良好な製品を得ることができる。According to the present invention, there is provided a compound (pigment derivative) which exhibits excellent effects when mixed with an organic pigment to form a non-aqueous dispersion system. Accordingly, the pigment composition of the present invention containing this pigment derivative together with an organic pigment can be used with excellent pigment aptitude for various uses such as coatings, printing inks, plastic coloring, and printing. In a non-aqueous dispersion system for paints or printing inks, compared with a system using an organic pigment alone, the dispersion viscosity is reduced, good fluidity is exhibited, there is no color separation, and coloring power is high, and printed matter is high. Alternatively, it is possible to obtain a good product having good gloss of the coating film and high transparency.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０９Ｄ 11/02 Ｃ０９Ｄ 11/02 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification code FI C09D 11/02 C09D 11/02
Claims (5)
れてもよい炭素数２０以下の脂肪族炭化水素若しくは芳
香族炭化水素の残基を表すか、又は両者が一緒になっ
て、それらが結合する窒素原子とともに、さらに窒素、
酸素及び硫黄から選ばれる異項原子を含んでもよい複素
環を形成し、ｋは１〜６の整数を表し、ｍは０.5〜３、
そしてｎは０.5〜３.5の数を表すが、ｍとｎの合計は１
〜５である）に相当するスルホンアミド化アゾ化合物。1. A compound of the formula (I) (Wherein, R 1 and R 2 each independently represent a residue of an aliphatic hydrocarbon or an aromatic hydrocarbon having 20 or less carbon atoms which may be substituted, or Together with the nitrogen atom to which
Forming a heterocyclic ring which may contain a heteroatom selected from oxygen and sulfur, k represents an integer of 1 to 6, m is 0.5 to 3,
And n represents a number from 0.5 to 3.5, and the sum of m and n is 1
To 5).
ド化アゾ化合物を含有することを特徴とする顔料組成
物。2. A pigment composition comprising an organic pigment and the sulfonamidated azo compound according to claim 1.
対して０.5〜３０重量％存在する請求項２記載の組成
物。3. The composition according to claim 2, wherein the sulfonamidated azo compound is present in an amount of 0.5 to 30% by weight based on the weight of the organic pigment.
又は３記載の組成物。4. The pigment according to claim 2, wherein the organic pigment is a condensed azo pigment.
Or the composition according to 3.
242である請求項４記載の組成物。5. The pigment according to claim 1, wherein the condensed azo pigment is CI Pigment Red.
5. The composition according to claim 4, wherein the composition is 242.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP02712198A JP4207236B2 (en) | 1998-02-09 | 1998-02-09 | Condensed azo pigment derivative and pigment composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP02712198A JP4207236B2 (en) | 1998-02-09 | 1998-02-09 | Condensed azo pigment derivative and pigment composition containing the same |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008034309A Division JP4438874B2 (en) | 2008-02-15 | 2008-02-15 | Condensed azo pigment derivative and pigment composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11228858A true JPH11228858A (en) | 1999-08-24 |
| JP4207236B2 JP4207236B2 (en) | 2009-01-14 |
Family
ID=12212236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP02712198A Expired - Lifetime JP4207236B2 (en) | 1998-02-09 | 1998-02-09 | Condensed azo pigment derivative and pigment composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4207236B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1167460B1 (en) * | 2000-07-01 | 2004-05-06 | Clariant Finance (BVI) Limited | Process for the preparation of disazo condensation pigments in microreactors |
| JP2005248127A (en) * | 2004-03-08 | 2005-09-15 | Toyo Ink Mfg Co Ltd | Pigment dispersant, pigment composition containing the same and pigment dispersion |
| JP2011094075A (en) * | 2009-10-30 | 2011-05-12 | Kao Corp | Water dispersion for inkjet recording |
| JP2011153280A (en) * | 2010-01-28 | 2011-08-11 | Fujifilm Corp | Fine pigment particle dispersion, photocurable composition, color filter using the same, dispersion auxiliary using the same, and method for producing the same |
| JP2012121983A (en) * | 2010-12-08 | 2012-06-28 | Dainichiseika Color & Chem Mfg Co Ltd | Pigment dispersant, pigment composition, pigment colorant, and colorant for color filter |
-
1998
- 1998-02-09 JP JP02712198A patent/JP4207236B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1167460B1 (en) * | 2000-07-01 | 2004-05-06 | Clariant Finance (BVI) Limited | Process for the preparation of disazo condensation pigments in microreactors |
| JP2005248127A (en) * | 2004-03-08 | 2005-09-15 | Toyo Ink Mfg Co Ltd | Pigment dispersant, pigment composition containing the same and pigment dispersion |
| JP4507643B2 (en) * | 2004-03-08 | 2010-07-21 | 東洋インキ製造株式会社 | Pigment dispersant, pigment composition containing the same, and pigment dispersion |
| JP2011094075A (en) * | 2009-10-30 | 2011-05-12 | Kao Corp | Water dispersion for inkjet recording |
| JP2011153280A (en) * | 2010-01-28 | 2011-08-11 | Fujifilm Corp | Fine pigment particle dispersion, photocurable composition, color filter using the same, dispersion auxiliary using the same, and method for producing the same |
| JP2012121983A (en) * | 2010-12-08 | 2012-06-28 | Dainichiseika Color & Chem Mfg Co Ltd | Pigment dispersant, pigment composition, pigment colorant, and colorant for color filter |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4207236B2 (en) | 2009-01-14 |
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